Catalytic Arene H/D Exchange with Novel Rhodium and Iridium Complexes
Organometallics2012Vol. 31(5), pp. 1943–1952
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Jennifer L. Rhinehart, K.A. Manbeck, S.K. Buzak, G.M. Lippa, William W. Brennessel, Karen I. Goldberg, William D. Jones
Abstract
Three novel pendant acetate complexes, [Rh(bdmpza)Cl3]−M+, [Rh(bdmpza)Cl2(py)], and [Ir(bdmpza)Cl3]−M+ (bdmpza = bis(3,5-dimethylpyrazol-1-yl) acetate, M+ = Li+, Na+), were synthesized. Abstraction of halide from these complexes with silver salts yielded species capable of C–H activation of arenes. The catalytic H/D exchange reaction between benzene and trifluoroacetic acid-d was optimized, and these conditions were used to evaluate H/D exchange in other arenes. Branched alkyl substituents in alkyl aromatics showed an affinity toward deuterium exchange in the β-alkyl position only. DFT calculations were performed to determine the mechanism of H/D exchange.
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